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Get a Motu M4 which has (so far) the best measured ADC performance below $500. The best one would be the RME ADI-2 PRO fs but that is expensive - OTOH it's more than 10 times cheaper than @amirm's AP.
I am a big fan of used gear, and have had much success on Craigslist. If I am looking at digital scopes, what is/are the key things I should look for to determine suitability?
12 or 14 bit ADC resolution. Most affordable DSOs have only 8 bits, and I don't think you get 16 bit for cheap money, even used (if it exists at all). Owon makes DSOs with 12 and 14 bit ADC resolution (XDS2102A 12 bit, XDS3064AE 14 bit) but I have no clue if they are any good or reliable.